[The Guy]

I am trying to synthesis the attached molecule. Starting material: CuI, NaN3, 2-bromothiophene, Propargyl alcohol, ligand(dimethyleethylenediamine) DMSO as rxn media.
Work up: add Sat NH4Cl, and DI Water, then extract with EtOAc
I end up with emulsion look too similar to:
It is even worse, but look similar even in color.
When I extract with THF the emulsion became less issue, but I end up extracting different substance.
Why it looks so bad with EtOAc? Even Brine has no effect on that. The emulsion is like a sponge and it spread all over the organic layer, unless the organic layer 10 times more than the aqueous layer, I would have some room to extract something each time.
Also, each time the aqueous layer smells like EtOAc, it always has alot of the solvent, I am afraid the product too.
Any suggestion?

[discodermolide]

How much DMSO are you using?

[The Guy]

2mL 

[discodermolide]

Do you filter the reaction mixture first?
Try a different solvent for extraction, isopropyl acetate or even dichloromethane

[The Guy]

Do you filter the reaction mixture first?
Try a different solvent for extraction, isopropyl acetate or even dichloromethane

If I did, the filter funnel will be clogged, and when I used vacuum filtration everything come it as it is.
I did try chloromethan, the desired product has low solubility in it, too low.
I will try isopropyl aceetate, I hope we have it in lab.

Thanks for your help.

[discodermolide]

You have an alcohol, try and acylate it first then extract. This will make it more soluble. You can then get it out pure as the acetate.
Hydrolyse the acetate.

[408]

Filter through kieselguhr with vacuum.  Rinse kieselguhr with lots of EtOAc and water.  Continue as normal.

[The Guy]

You have an alcohol, try and acylate it first then extract. This will make it more soluble. You can then get it out pure as the acetate.
Hydrolyse the acetate.

You mean more soluble in CH2Cl2?

[The Guy]

Filter through kieselguhr with vacuum.  Rinse kieselguhr with lots of EtOAc and water.  Continue as normal.

I am not sure if the reagents has something to do with the emulsion, however, I will try your suggestion.
I really appreciate your help guys

[408]

Fine suspended particles often make for horrible emulsions.  Removing them helps as long as you make sure to remove any stuck product with lots of washes. 

[The Guy]

I want to thank your for your golden comment. After vacuum filtration through Celite the emulsion and the whole extraction process has been resolved, with EtOAc the emulsion still exist but a little things that I could overcome, with other solvents it disappear.

Thank you for helping me.